Small Steps Create Big Shifts
The Small Business 1099 & W-2 Survival Guide: How to Conquer Your 'January Receipt Mountain'
Be honest: Is there a stack of receipts, invoices, and random paperwork sitting in the corner of your desk right now? Maybe it's in a shoebox. Maybe it's spread across three different folders on your laptop. Or maybe—and we say this with zero judgment—it's just... everywhere.
Welcome to the January Receipt Mountain. Every small business owner knows it well.
The good news? You're not alone. The better news? That mountain can absolutely be conquered before tax deadlines hit. You just need a game plan.
This guide will walk you through everything you need to know about filing 1099s and W-2s, gathering the right documentation, and getting your books closed out cleanly. Let's knock that receipt mountain down together.
Why January Feels Like Financial Chaos
January is crunch time for small businesses. You're trying to start the new year strong while simultaneously closing out last year's books.
- You need to report what you paid people last year (employees and contractors)
- You need accurate records to file those reports correctly
- The IRS has firm deadlines and they don't care about your busy schedule
The Big Question: Who Gets a 1099 vs. a W-2?
This is where a lot of business owners get tripped up. Let's break it down simply.
W-2: For Your Employees
If someone works for you as an employee, they get a W-2. This applies to full-time staff, part-time staff, and anyone whose work schedule, tools, and methods you control.
1099-NEC: For Your Independent Contractors
If you paid an independent contractor $600 or more during the year, they get a 1099-NEC. Contractors control how and when they work and are responsible for paying their own self-employment tax.
The W-9 Secret: Get This First, Pay Second
Pro tip: Never pay a contractor until you have their W-9 on file. This form collects their legal name and TIN. Without it, you literally cannot file their 1099 correctly.
Checklist: What You Need to File
For W-2s: Full legal name, address, Social Security number, total wages, and all taxes withheld.
For 1099-NEC: Contractor’s legal name, address, TIN (SSN or EIN), and the total amount paid.
Mark Your Calendar: The Real Deadline
This year, January 31 lands on a Saturday. That means the actual deadline is Monday, February 2.
| Form | Send To | Submit To |
|---|---|---|
| W-2 (Copy B) | Employees | N/A |
| W-2 (Copy A) + W-3 | N/A | SSA |
| 1099-NEC (Copy B) | Contractors | N/A |
| 1099-NEC (Copy A) | N/A | IRS |
How to Actually Conquer the Mountain
- Gather Everything: Collect receipts and statements into one spot.
- Separate Lists: Categorize employees vs. contractors.
- Verify W-9s: Ensure you have info for every contractor paid $600+.
- Confirm Totals: Cross-reference with bank statements.
- Generate & File: Submit electronically before February 2nd.
When the Mountain Feels Too Big
We help small businesses and nonprofits get their books in order and file everything on time—with zero judgment. That’s the High Point difference.
Ready to Knock Down That Mountain?
Don't let the February 2nd deadline stress you out. We'll help you file correctly.
Schedule a Free Consultation